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Nucleic Acids Symposium Series 2005 49(1):173-174; doi:10.1093/nass/49.1.173
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© 2005 Oxford University Press

Modification of the aromatic ring of the WNA analogues for expansion of the triplex recognition codes

Yosuke Taniguchi1, Ayako Nakamura1, Eriko Aoki1 and Shigeki Sasaki1,2

1 Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan, 2 CREST, JST

Triplex-forming oligonucleotides (TFOs) are powerful tools for genomic research. The most stable triplex is formed by the interaction between TFOs and homopurine/homopyrimidine sequences in the target duplex, but the triplex DNA is hampered by one pyrimidine base in the homopurine tract. Previously, we developed novel nucleoside analogues (WNA: W-shaped nucleoside analogues) to recognize pyrimidine/purine inversion sites (TA or CG interrupting sites) and determined two useful WNA analogues, WNA-ßT and WNA-ßC. However, subsequent study showed that the triplex formation using the WNA analogues was dependent on its neighbouring bases of the TFOs. In this study, the new WNA analogues having a different aromatic ring were synthesized to evaluate effects on sequence dependency. It has been found that o-bromo, m-bromo-, and p-cyano- substituted WNA-ßT derivatives are selective to a TA interrupting site to form triplexes with high stability in the sequences where original WNA-ßT could not recognize.


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